Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:37:13 UTC |
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Update date | 2015-07-21 06:57:57 UTC |
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Primary ID | FDB023946 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Lumisterol 3 |
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Description | Lumisterol 3 is a normal human secosterooid metabolite from the class of vitamin D3 photoisomer derivatives. It is synthesized from 7-Dehydrocholesterol in the epidermis in response to ultraviolet irradiation. When human skin is exposed to ultraviolet radiation, epidermal 7-dehydrocholesterol is converted to previtamin D, and during prolonged exposure, the synthesis of previtamin D3 reaches a plateau at about 10 to 15 percent of the original 7-dehydrocholesterol content, and previtamin D3 is photoisomerized to two biologically inert isomers and lumisterol 3 is one of them (the other one being lumisterol 3). Therefore, lumisterol 3 is a metabolite to chronic exposure to sunlight. Lumisterol 3, as well as other photoisomers of vitamin D3 and previtamin D3 has been demonstrated to have inhibited keratinocyte proliferation. Thus, sunlight provides vitamin D3 photoproducts that may act directly to regulate epidermal proliferation and differentiation under physiologic conditions. (PMID 6256855, 10876100) [HMDB] |
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CAS Number | 5226-01-7 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C27H44O |
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IUPAC name | (1R,2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol |
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InChI Identifier | InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1 |
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InChI Key | UCTLRSWJYQTBFZ-XMVWLVNMSA-N |
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Isomeric SMILES | [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C |
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Average Molecular Weight | 384.6377 |
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Monoisotopic Molecular Weight | 384.33921603 |
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Classification |
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Description | Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Cholestane steroids |
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Direct Parent | Cholesterols and derivatives |
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Alternative Parents | |
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Substituents | - Cholesterol
- Cholesterol-skeleton
- 3-hydroxy-delta-5-steroid
- 3-hydroxy-delta-7-steroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- Delta-7-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Lumisterol 3, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ar0-1019000000-eadea32647b1133f9515 | Spectrum | Predicted GC-MS | Lumisterol 3, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002f-3005900000-c63a75d6ed190e98a35b | Spectrum | Predicted GC-MS | Lumisterol 3, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0019000000-d2b535e3c3ed257f2215 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ar9-3139000000-87132b4b12416fa4f01e | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-5249000000-257a8915fd5fab2dfaaa | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-8ff4cced50a3c638abba | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0009000000-6d9a73d8f487e848e538 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ldi-1019000000-eb1f58f2c9df95716640 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0009000000-5cafb4a46516e1c4ca5a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ktr-9168000000-27f4addc4e70c9e3fc88 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9510000000-fce215a9f0a5b16bb81c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-0009000000-cf419f92ab7dfef8f2f8 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 99690 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 111049 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB06505 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 2288990 |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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